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8 years ago I decided that whatever startup I was going to launch would be the last startup I ever did.

I made this decision after launching 8 startups and realizing that creating a company as a "means to an end" was a shitty way for me to live.

I found myself in this constant cycle of being wildly preoccupied by "the next thing." Raising money for my startup was a means to a quicker exit. Killing myself meant I could finish this chapter faster, more successfully.

I had endless justifications for compromising my life because I could always "make it up later."

But what if there was no "later"?

This time around I decided to change it up.

I asked myself, "What if I picked what I wanted to do for the rest of my life NOW?" So instead of maki...

During the early days of my first startup I stumbled upon a huge liability that was killing us quickly — me.

What's funny is no one else needed to have this discovery. The rest of the organization had figured out long ago that I was immature, combative, prone to anxious tirades, and generally a pain in the ass to work with.

And looking back, I'm probably being kind.

As a Founder (and CEO), every single one of those idiosyncrasies becomes amplified a hundred-fold because my liabilities to the organization become rooted in every decision we make, every interaction we have, and the entire morale of the company.

If we don't exercise some serious self realization — and do it quickly — we may be creating one of the biggest hurdles our organiza...

There's an incredible amount of magic in having very little time to get things done.

That's why at Startups.com, with over 200+ people, we manage our entire workload based on what we plan on getting done by Friday. That's it. No long term planning sessions, no confusing Gantt charts or Trello boards. Just 5 days to get stuff done.

And damn it's effective.

Less Time = Less Room for Excuses

The problem with creating longer planning cycles is that every additional day, week, or month decreases the visibility and accountability for a single day of work. Our focus needs to be reducing the amount of time we can cheat on our time.

Imagine we wanted to lose 10 pounds this year. At lunch, we can order a cheeseburger, because hey, we have all year t...

While the novelty of creating the next Facebook sounds amazing, the truth is we don't need to necessarily invent a product to bring a new innovation to market.

If we look closely, we'll see that some of the fastest-growing companies out there — Uber, Casper, Dollar Shave Club and dare I say it, WeWork — are all based on ancient business models with a new twist.

Start With This: "What's Wrong With Current Products?"

Look, Uber didn't invent taxis — they just simply asked, "What's broken about the taxi business?" (Well, the limo business initially but who's tracking?) Any of us would be hard-pressed to find an existing product or service that couldn't use a ton of improvement.

Startups feel like sprints in the beginning, but for any of us who have done this before, we've learned that it's a marathon.

We're judged by our speed when we start — and our endurance when, and if, we finish.

When Does "Pacing" Ourselves Start to Matter?

Not in the beginning. In the beginning, it's full sprint all the time — or at least that's the way it feels. We've got a headful of energy and we're ready to tackle every problem with longer nights and more stress.

But it doesn't take more than a year or two before those late nights and sustained stress start to run us down. Getting fired up over every last problem, and the stress that comes with it, begins to burn our cortisol levels to a dangerously low point.

For nearly 3 decades, if you asked me how many hours I work, I would just say "All of them." I wore it as a badge of honor. For almost 20 years it never occurred to me that you could drive to or from work in daylight. For my first three years of my startup career I didn't see my family or celebrate Christmas.

Now let me admit what a colossal flipping waste of energy that was.

Yes, I created great startups and had some success. Yes, a lot of that "hard work" was necessary. But now, with the benefit of history and having watched thousands of startups go from zero to something, I've come to learn something:

Those long hours were a symptom of inefficiency, not a default badge of honor ...

We're worried that employees, investors, customers and just about anyone else will think less of us. Maybe they won't invest, maybe they won't buy our products, or maybe they won't come to work for us.

Sharing our flaws is terrifying. But it's also one of the most liberating things we can do not just as Founders, but as the weirdo humans we all are.

You're the Founder/CEO of Startups — do you have flaws?

Geez, where do I begin?

I've been building startups for nearly 3 decades and I have tons of flaws. I've got massive ADHD (I can't even proofread this sentence without losing focus), terminal pain, crippling anxiety — and I can't dance to save my life.

Imagine what would happen if we spent as much time trying to teach kids to become entrepreneurs as we did trying to get them to prepare for the SATs?

Let's remember that a disproportionate amount of our academic focus is around a series of standardized tests designed in an era where homogenizing the workforce was our number one goal (side note: it worked).

Now our goal is the polar opposite: differentiating our workforce. The only way our kids will succeed is if they can stand apart from others and chart their own course.

That's the essence of entrepreneurship, and it's something we can absolutely teach.

Why should we start with kids as entrepreneurs?

Getting equity back from an existing stakeholder isn't easy — but it is possible.

It's a situation that very few Founders have ever been through before, so no one really knows how to go about it. Let's talk a bit about how the situation develops and what we can do to get some of that precious equity back into our coffers.

Remember, Equity is a Promise of Payment

More than anything, equity isn't just a stock issuance. It's a promise that at some future point that stock will be worth cash money — maybe.

When we think about pulling the equity back, we have to think in terms of how to redeem that promise of payment in some capacity. It's not just a matter of "taking it away" per se, it's a matter of trading the terms of the initial agreement ...